Showtime With The Boss – From Str8 to Sissy on Cam

**Intro**

So this is the first part of a story I wrote. And if you like it, feel free to take this as a roleplay prompt and message me!

**The Best Plans are No Plans**

It was Friday night and I didn’t have any plans, so I figured I’d do what I always did when it was Friday night and I had no plans… have a few beers, play Xbox for a while, and then browse the internet for a while until eventually browsing my way to some porn to jerk off to.

My roommates Jay and Tyler had tried to cajole me to come out to party with them tonight but I just wasn’t into the vibe of the noisy college bar they wanted to go to. Even during the summer when most of the students in town were gone, it would still get especially crowded on Fridays with students like us that kept their off campus apartments year round. Eventually I delayed enough where the guys took off without me and I had the apartment to myself to relax.

Hot for Teacher [FF, Fdom, NC, MC] (part 9, final-part)

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**Conclusion**

It had been almost a week since Michelle had been brought to Lisa’s for training on how to be the perfect lesbian lover and while the young school teacher had been forced to have non-consensual sex: drugged, blackmailed, and dominated by other women, she now embraced this transition in her life. It was almost as if the Michelle who existed before last Friday was gone and a new version simply took her place.

Michelle would never be able to adequately convey the new feelings she had or share with others the profound change in her life, but she knew it was as if a light were shown for the very first time that removed any darkness. Her life had become clear and she knew exactly what she really wanted – not what others had told her she should expect and be content with.

She had tasted of the fruit and now she wanted to devour and savor its essence. Kim had shared with Chel that neither she nor Lisa had ever drugged another woman before. Lisa much preferred the art of seduction but that time demanded it and they knew Chel would be resistant to embracing the change she needed in her life.

Straitjacket fantasy [25M] [consensual] [bondage] [missionary]

Mesmerizing red hair, pale and flawless white skin, crimson red lips curled in a devious smile and emerald green eyes stare at me, blinking quickly in anticipation. She lays on the queen-sized bed, staring at me in nothing but her tight leather leggings, which highlight her perfect behind and her black bra. As I approach her, I reveal what I have hidden behind my back: A red collared Posey straitjacket. She bites her lower lip in anticipation, her gaze says it all: “Tie me up , daddy”.

She walks towards me, her hips swaying playfully with every step, until she’s met with the jacket’s warm embrace and the most delightful feeling of helplessness. I strap her in, sweetly caressing her waist, her breasts and her legs as I strip her off her arms. When she’s finally giving herself the tightest hug possible, I sit her on the mattress and position myself behind her. I kiss her cheeks and work my way up to her lips. I teasingly go down to her neck and she starts to struggle a little, begging me to go all the way, but I deny her request for release. I start to rub her nipples over the jacket; my fingers making a thousand promises of pleasure to come. I kiss her neck again, ever so gently, so tenderly, trying to hold in the raging, lustful monster inside me. I slide my right hand all the way to her crotch, rubbing it subtly. My other hand ventures under the jacket to pinch her hardened nipples, one at a time.

Straitjacket fantasy

I’ve always wanted to tie a girl up in a Posey straitjacket. Or any other straitjacket would be fine, but the Posey ones are my favorite. I just need to get the jacket… and a girl who wants to be tied up in one.

I’d strap her up before bed, sweetly caressing her waist, her breasts and her legs as I do so. When she’s finally giving herself the tightest hug possible, I’d sit her on the mattress and position myself behind her. Then I would kiss her cheeks and work my way up to her lips, then would teasingly go down to her neck and she starts to struggle a little, begging me to go all the way, but I resist. I start to rub her nipples over the jacket; my fingers making a thousand promises of pleasure to come. I kiss her neck again, ever so gently, so tenderly. Then I’d slide my right hand all the way to her crotch, rubbing it subtly. My other hand ventures under the jacket to pinch her hardened nipples one at a time.

Girlfriend brutally humiliated and exposed in front of everyone (ENF) (Fiction) (Public)

Before I start let me just say that although this story isn’t true, all my stories are based off real people, and jenny actually is my girlfriend. She does know I love humiliation and exposure and she enjoys teasing me in school with it. PM me if you want to see what jenny and Miranda look like or if you want to hear more stories, some of which are real, and what jenny does in school. My girlfriend Jenny (F18) just graduated highschool and this is an event right before lockdown. Shes 5,3, with brown hair, good sized tits, not skinny but nowhere near fat and she’s pretty thick. Jenny’s one of those girls who’s usually confident and never flustered, she’ll also be brutally honest and has the reputation of being bitchy and is never afraid to speak her mind. I think you get the type? Anyways jenny got in an argument with this other girl Miranda, because jenny called her a dumbass. Mirandas 5,5 with a similar body style but nowhere near as thick with blonde hair. The argument escalated into a screaming match and then Miranda slapped jenny across the face. Jenny stepped back in shock and Miranda slapped her a few more times. Jenny slapped her back and then Miranda answered with a punch to face. Jenny was clearly rocked and stumbled back and fell on her back. Miranda then stood over her and grabbed her shirt to pull her up and slap her. When Miranda bent her asscrack peeked out of her jeans and when she pulled jenny’s shirt it stretched and jenny’s tits were completely exposed. A couple more slaps and punches and jenny kicked her off and tried to run. Jenny was running with her tits still hanging out and bouncing, when Miranda tackled her from behind football style, which caused jenny’s baggy sweatpants and underwear (white thong with pink hearts) to fall around her knees. Jenny’s bare ass was seen by everyone, her pussy was showing too (she hadn’t gotten around to shaving in a bit too) for a brief second. They struggled on the ground and rolled over each other and Miranda got to her feet . Jenny started crying and begging for her to stop. I thought it was so hot seeing my confident, never flustered bully girlfriend, on her knees begging for mercy and exposed in front of everyone. Miranda didn’t hesitate to kick her in the head, knocking her out her head fell forward on the floor and her ass went out. She was literally face down ass up doggystyle with her cheeks spread and her whole fucking asshole on display. Then Miranda bent over screaming insults in her face , but her jeans had come undone and she was showing a good amount of plumbers crack, half mooning everyone before she got dragged away by the gym teacher on lunch duty.

Idea

My sister has a friend named Monique. Black with 34DDD tits. She came to the house the other day in a very skimpy bikini and was flaunting her tits like no one’s business. I had to go inside and fap to her through the window. On her Insta she posts all these photos of her in skimpy bikinis and then she comes over and hangs out with my sister…. flaunting that ass and that arch that would make Mia Malkova blush…. I need to fuck this girl….

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So yeah someone write a story where I plow her ass and fuck her tits. My name is Alex

Tennis Shoes Girl [baited, semi-consent, fiction, age-gap]

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My apartment building is an old hotel with a staircase that goes up eight stories. It takes a few minutes to walk the whole thing, which I like to do instead of taking the elevator.

Each flight is a little too tall between landings, and a couple of times, in the hot months of the summer, I’ve encountered a woman in a skirt coming down while I was going up. Both times, I could tell that they felt unexpectedly exposed. They would squeeze their thighs together and shuffle as quickly past me as possible. Me being 6’4”, 215 pounds, athletic and very not-white, it’s not a totally unexpected reaction. And I’m not proud to say that I get a twinge of satisfaction when small women get a little tense around me. Lucky for me, I’m also very handsome, and have a deep, kind voice – so a smile and a “hey” usually puts them at ease. A little.

Subliminal Broadcaster 2000 Pt. 3 [Hypnosis, Anal, Orgy, Toys]

(This story is inspired by CryptoKnight’s excerpts on Literotica. You can find the first two stories [here](https://www.literotica.com/s/subliminal-broadcaster-2000?page=2) and [here](https://www.literotica.com/s/subliminal-broadcaster-2000-ch-02).Thanks for reading!)

Andy woke up naked to the warm sensation of lips closing around his cock. He opened his eyes and saw Michelle Fowler’s bald head bobbing up and down on his crotch. Her chains rattled as she worked to jerk him off, desperately craving her morning cum.

It wasn’t just the two of them in bed. Blindfolded and gagged next to Andy was Theresa Herman, the blonde highschool senior from down the block. She still wore her stained cheerleader’s outfit, the set she had on when Andy picked her up from practice.

“Wow Mr. McGregor, those inspirational disks you gave me were amazing! They really helped me overcome my pregame jitters.” Andy knew his tapes were successful when Theresa bent over to put her backpack in the trunk, revealing her lack of panties.

His invention, the SB “Subliminal Broadcaster” 2000, broadcasted at a frequency just barely beyond human awareness. The messages were too low to be heard consciously, but they would assail themselves strongly on the subconscious level. After listening to the innocent CDs, the subject believed that the messages being broadcast by the SB 2000 were his or her own thoughts.

Getting dirty with the maid (MF)

Only a few days after my return from my freshman year of college, I was already bored with being home. I immediately missed the partying and the girls while i killed time in my quiet suburban town between shifts in my summer job.

After a pretty late night out at the movies with friends, I slept in the next morning. In the mornings, my parents usually were busy and didn’t really bother me, trusting I can handle my own schedule.

I took a quick shower, and was walking into my bedroom, naked and deciding whether it was too early for lunch, when a voice cut across my thoughts.
“Um… good morning.”

I froze. Next to my dresser, Elena, the women who cleaned our house weekly, stood with a duster in her hand.

Immediately, a million thoughts ran through my mind. Should I cover up or go grab a towel? She was next to my dresser, so I felt weird walking over to get underwear.

“Shit, I forgot today is Thursday. I’m sorry.” Her expression still showed surprise, but definitely didn’t look away. After my shower, the room felt embarrassingly cold.

She Isn’t Boring Anymore! Metamorphosis of a Hot Wife

She didn’t say a word, instead, she unbuckled her seatbelt, leaned over into his lap, unbuttoned his pants, and jerked his cock from the cotton fabric that held it. She teased the tip with her tongue and he instantly grew. She wrapped her lips around it and bobbed her head up and down. He looked down and only saw her bright blonde hair as she sucked him hard and fast. She felt his legs begin to shake and that made her go even faster. Within two minutes her mouth was full of cum. She raised her head up, looked at him and swallowed. She opened her mouth to show that it was all gone.

Tyler moaned, “Holy fuck! What have you done with my wife? Where is she?!”

They both laughed as Michelle sat back in her seat. A droplet of cum managed to escape her mouth and was about to drip off her chin. She felt it at the same time her husband saw. She smiled as she used her index finger to clean it off and slowly, and sexily, licked her finger. She winked at him as she swallowed again.